Acetalsof propargyt abc



Patented Aug. 7, 1 951 STATS QEFI-CE ACETALS F PROPAHGYL' ALCOHOL Frederick Fahnoe, Easton, Pa., assignor to General Aniline & Film Corporation, New York, N. Ya, a corporation of Delaware No Drawing. Application December 16, 1948, Serial No. 65,713-

8 Claims. I. This invention relates to new compounds and the process for preparing them.

These new compositions have the following-general formula:

OCHQCECH R\ 'oonzozonr wherein-R is an aldehyde functional group including aliphatic, aromatic and heterocyclic aldehydes.

The process for preparing these compounds comprises generally refluxing propargyl alcohol with the desired aldehyde. In the case of formaldehyde, the reaction may be represented as follows:

oonlozon CHiO 2CHECCH2OH=CH2 OCHzCECH The following example illustrates the preparation of some of the compounds falling within the scope of this invention, but it will be understood that the invention is' not limited thereto.

Example A mixture of pure propargyl alcohol with an excess above a stoichiometric amount of a 30% aqueous formaldehyde solution is refluxed for a few minutes and then distilled. The pot residue was dipropargyl formal and the yield was about 20% of the original propargyl alcohol. Dipropargyl formal has the following formula:

OGHzCECH and this is borne out by the following analytical data:

Observed Theory 0 as dipropargyl formal 67.76% 67.77% H as dipropargyl formal 6. 81 6. 45 Unsaturation (Moles/moles formal)- 4. 02 4. 00 Acetylem'c hydrogen per mol formal 1.90 2.00 Refractive index at 25 C s 1. 4430 B. P. at 760 mm. Hg .C" 174 The product hydrolyzes extremely slowly in acid solution, which is unlike most acetals. It is water white.

In general, these acetal derivatives of propargyl alcohol may be formed with any aldehyde such as, for example, aliphatic aldehydes (acetaldehyde, propionaldehyde, butyraldehyde), aromatic 2. aldehydes (benzaldehyde, cinnamonaldehyde, vanillin, naphthaldehyde, methoxybenzaldehyde), heterocyclic aldehydes' (furfural) Examples; of other; compounds which may be 1 formed from thesealdehydes include, for ex-,

ample,- dipropargyl 'benzal, Whichha the. follow.- ing formula;

0 CHzCECH o CH2 CECE and dipropargyl furfural, which has the following formula:

wherein R is a halogen-free residue of an aldehyde.

2. A new composition of matter comprising a compound having the following formula:

oomozon o CHiCECH wherein R is a halogen-free residue of an aromatic aldehyde.

3. A new composition of matter comprising a compound having the following formula:

wherein R is a halogen-free residue of an aliphatic aldehyde.

4. A new composition of matter comprising a compound having the following formula:

0 CH2 CECH O CHzCEOH wherein R is a halogen-free residue of a heterocyclic aldehyde.

5. A new composition of matter comprising a dipropargyl formal of the following formula:

OCHzCECH OOHICECH 6. A new composition of matter comprising a compound having the formula:

O CHzCECH wherein R is a residue of an unsubstituted alde- 7. A new composition of matter comprising a compound having the following formula:

0 CHzCECH O CHzCEOH 8. A new composition of matter comprising a compound having the following formula:

HCH

FREDERICK FAHNOE.

E O CHzCEOH 0 REFERENCES CITED The following references are of record in the file of this patent:

UNITED STATES PATENTS Number Name Date 2,411,826 Filachione Nov. 26, 1946 OTHER REFERENCES Sabatier: Catalysis in Organic Chemistry (1922), pages 779-783.

Adams et al.: J. A. C. S. 47, 1358-67 (1925). 

1. A NEW COMPOSITION OF MATTER COMPRISING A COMPOUND HAVING THE FOLLOWING FORMULA: 